Chiral Recognition of N-.ALPHA.-Acetyltryptophans with Molecularly Imprinted Polymeric Membranes Containing DVNE Derivatives.

Abstract

Molecularly imprinted polymeric membranes,

Molecularly imprinted polymeric membranes having EFF derivatives as a chiral recognition site

“…1, and those reported previously [27][28][29][30][31][32][33] , it can be said that the chiral recognition site toward L-isomer was formed by the presence of the print molecule Ac-L-Trp during the membrane preparation process. 1, Fig.…”

“…The adsorbed amounts are given not only in absolute but also in relative values which are based on the EFF derivative for convenience in the following discussion. Therefore, the present membrane having a tripeptide derivative as a chiral recognition site also gave adsorption selectivity like those with a tetrapeptide derivative [27][28][29][30][31][32][33] . 1, the results summarized in Tab.…”

“…This led us to develop an alternative molecular imprinting technique [27][28][29][30][31][32][33] , that is, the "molecular memory" of the target molecule is introduced in the membrane at the same time that the polymeric construction is prepared from the polymer solution. In this case, the conventional molecular imprinting technique is not suitable to impart molecular recognition sites in synthetic polymers.…”

Effect of constituting amino acid residue numbers on molecularly imprinted chiral recognition sites

“…Some membranes prepared in the present study, of which constituting amino acid residue numbers of three to six, showed adsorption selectivity toward the L-isomer, like the molecularly imprinted polymers from tetrapeptide derivatives. 19 From the previously reported data, 8,[20][21][22] it is known that the polymer prepared in the absence of a print molecule does not show a chiral recognition ability. The molecularly imprinted polymers from D-resin, DI-resin, DIDEDID-resin, and DIDEDIDE-resin hardly showed adsorption selectivity.…”

Alternative molecularly imprinted membranes from a derivative of natural polymer, cellulose acetate

“…It is necessary to introduce physical stereoselectivity into synthetic membranes so that they can separate mixtures of optically active compounds. The authors adopted oligopeptides, 23,25,27,30,33,34,36 a derivative of natural polymer, 31 and nonchiral synthetic polymer 35 as candidate materials to form chiral recognition sites; these materials were converted into chiral recognition sites toward amino acids or amino acid derivatives by applying an alternative molecular imprinting technique. That is, molecular memory of the print molecule, which is separated or recognized, is introduced in the membrane simultaneously while the polymeric membrane is prepared from its polymer solution (i.e., membrane preparation with simultaneous molecular imprinting).…”